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Cartilage Free Captain grades Tottenham’s January 2024 transfer window

SPOILER: it was good!

Tottenham Hotspur v Brentford FC - Premier League Photo by Marc Atkins/Getty Images

The dust has settled on the January transfer window, so it’s past time to actually take a good look at what Tottenham Hotspur accomplished in January. And to be frank, it’s somewhat astonishing. Spurs were one of only a few Premier League clubs that made serious purchases in the window. Johan Lange and Spurs’ new recruitment team had a plan, implemented it, pivoted when required, and ended up with Radu Dragusin, Timo Werner, and a summer signing of Lucas Bergvall when all was said and done.

As we do every window, I asked members of the Carty Free masthead to think about Tottenham’s business in this window, reflect on it, and assign a letter grade (American style) to how they think Tottenham did. Our answers are below. Add yours in the comments.

Dustin George-Miller

Tottenham Hotspur doesn’t do January transfer windows. January windows are for cheap, opportunistic pick-ups and to save struggling teams from relegation, not to make targeted, long-term, strategic decisions. And yet this window, as with last January, that’s exactly what Spurs have done, setting themselves up for the future with the signing of a young, athletic central defender (Radu Dragusin) who may not get many minutes in the short term but will feature in Ange Postecoglou’s future plans, especially if Spurs qualify for European competition.

Of course, Timo Werner’s loan is also 100% an opportunistic pick-up, a proven (if slightly bruised) attacker with Premier League experience who can patch the Son-shaped hole in the squad and provide valuable minutes in the stretch run. He may not be a long term solution, but I think thus far he’s already done enough to justify Spurs spending real money on him this summer.

Tottenham have been a hot mess in recruitment for so long, but Spurs shown ample evidence of a real plan — not just in first team recruitment (and early in the window), but players, like Lucas Bergvall, who very well may become part of the next great Tottenham Hotspur team and good developmental loans for players that need them to take the next step. Spurs’ prudent financial stewardship over the years has led them to where they’re the only team in the league that’s nimble enough to make serious purchases.

Tottenham Hotspur doesn’t do January transfer windows, but this time they did, and it was very, very good.

Grade: A

Matty Flatt

It’s hard to write about the January window without mentioning what it represents: that is, a club that has come from shambolic, ad-hoc, last-minute transfers, and no semblance of a plan to build for the future on the pitch... to a club with a new-look, data-oriented backroom staff taking the pressure of Daniel Levy (and yes, that includes Fabio Paratici!), and a club with the ability to spend smartly and appropriately due to years of clever commercial investment. While other clubs were hamstrung by FFP, Tottenham Hotspur set their targets, and went out and got them EARLY.

Timo Werner is an example of a no-lose transfer, providing valuable, experienced depth at little cost to the club, and with the ability to make the move permanent for a small fee. Radu Dragusin by all accounts was not our first choice, with the club linked heavily to Jean-Clair Todibo early in the window, but this was once more an example of our excellent processes as the club quickly pivoted to Romanian. Dragusin is athletic, young, and has the tools to succeed in Postecoglou’s system. Lastly, Spurs have looked to the future with Lucas Bergvall, beating Barcelona to the signing of the talented Swede.

That’s without even talking about the outgoings, where Spurs organized some fantastic loans for some of their youth and successfully moved some of the aging old-guard on to new lodgings. All that could have made this window better would have been to see the likes of Bryan Gil and Pierre-Emile Hojbjerg find a club more suited to their skillsets, and Spurs sign a nailed-on starter in one of their positions (i.e. an elite winger or midfielder). You can’t help but think the future is bright, the future is Lilywhite.

Grade: A

Sean Cahill

I’m not sure this window could have gone any better unless we bought Chelsea’s captain just for the banter. Dragusin is excellent depth behind Cuti and VDV while nabbing Timo Werner on a low-risk, high-reward loan is already paying dividends (three assists in three matches) for the squad. Throw in the expected pick-up of Bergvall today or tomorrow for the summer and getting a bunch of loans for growth is a heck of a way to close out January. I would have loved to see us get Gil out the door but we can’t win them all. In a window that is usually pretty quiet, Spurs were the ones wheeling and dealing for the stretch run of the season.

Grade: A


What a relief for Spurs to actually get all their business done in the English Premier League’s transfer window. Now, at long last, fitzie can finally give the club’s activity a rating.

It’s nice to see Spurs finally flex that financial muscle of theirs (much of which has been written about already), bringing us Radu Dragusin and, come summer, Lucas Bergvall. That loan + option to buy for Timo Werner looks very smart too.

But I’m more interested in the outgoings. We’ve got some much-needed turnover with the departures of Hugo Lloris and Eric Dier, Ivan Perisic and Djed Spence (who is hanging out in AnyWhereButTottenham).

Ash Phillips and Alfie Devine both got smart moves to Plymouth Argyle, with both receiving high praise. Meanwhile, we can expect Alejo Veliz to get plenty of playing time at Sevilla. Let’s also not forget Luka Vuskovic, another wonderkid who’s been loaned out to hopefully get some playing time.

Hopefully, by the time the 2026 US midterms roll around, we’ll see the fruits of this window come to fruition with a serious title push.

Grade: A